Don't lose focus. Just say no to the Jeep.
My needs are very similar to yours. I currently drive a 2009 Subaru Forester. Prior to that I had a Saab 92x (Saabaru) and a Tacoma. I drive a lot of dirt and gravel forest roads that are rutted as well as makeshift dirt kayak launches at the river. I tow a trailer with kayaks. My suspension is mush as a result. I had the struts replaced under warranty but that didn't help. Now that I am out of warranty I have an STI rear sway bar and Swift Springs in the garage ready for install. I can't imagine towing a heavier trailer on dirt / gravel with a Forester. The rear end is under damped to begin with and I don't think the drive train can handle the stress.
You need a truck!
My Tacoma sucked in the snow, until I added an A.R.E. cap. That balanced it out and it was as good in snow as any SUV with the right tires.
My next vehicle will be either a Tacoma or a Ridgeline.